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Elaine

"A chance opportunity to re-awaken a dream"

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Many years ago I had a brief affair.  I was then in my early forties, Elaine a bit younger.  We were both married.  While the sex at the time was both intense and very good, we both had lives full of other complications, and neither of us dealt well with the secrecy and sneaking around.  It didn't last.

In the years that followed, however, we kept in touch, talking on the phone, meeting for coffee and occasionally going for a walk.  Over the years we both had to deal with some serious life issues and found mutual support and comfort in each other when things grew dark.  In short, what started as a sexual fling, turned into something deep and meaningful.  We also became family-friends; inviting each other to celebration and parties, and even going out as two couples together.  Apart from still being married to other people, we have as close a friendship now as two people can.

Several months ago Elaine's uncle passed away.  He lived the other end of the country.  She of course went with her husband to the funeral but later found that she'd been named executor in his will.  From what I understood, her uncle owned very little and his last instructions were not exactly onerous, but it did mean she had to go back to see the family solicitor and sign documents.

This second trip fell at a time when Elaine's husband was busy at work, and having never driven very far on her own, she started to worry about the trip.  When she told me, I didn’t hesitate in offering to make the drive with her; it's what any good friend would have done, and our respective spouses accepted the suggestion as though it was the most obvious and natural thing in the world.  I knew before setting off that we would be staying two nights, giving her a full day for meeting the solicitor and seeing family, but it was while making the journey that Elaine told me the arrangements.

"Do you remember the sex we used to have," she asked, after sitting silent for a long while.

"I've aged by twenty years," I replied teasingly, "but I'm not senile yet.  Of course I remember."

"Do you miss it?"

"I don't miss the dirt and dust we put up with in that old house, and I don't miss getting splinters in my knees, but I do miss the sex.  We're neither of us as fit as we were, and I'm not sure I could manage all the things we tried to do back then, but..."  My mind wandered, partly on the junction we were approaching in the car, and partly on memories of the moments we had snatched together, the occasional grope, the quick fuck against the wall hoping no-one would walk through the door.

"I'm glad,"  Elaine said, her voice sounding unusually nervous. "Because I only booked one room at the hotel.  A double."

It was hard not to take my eyes off the road, or my hands off the wheel.  I apparently had the biggest grin on my face that she'd seen for years.  When I reached over, took Elaine 's hand, and lay it against my groin, I think I also had the biggest erection for years too.

Apart from the now heightened anticipation, the rest of the journey was uneventful.  It was early evening by the time we arrived, and we were both weary so after unpacking, freshening up, and phoning our respective spouses to say we were safe, we sat in the hotel bar and ordered food.  The conversation flowed as easily as it ever did between us, covering both what needed to be done the following day and the inconsequential stuff that friends discuss and laugh over.  It was when I said I thought we should order a bottle of wine, Elaine‘s voice sounded nervous again.

"You know the hospital changed my medication?"

"Yes," I answered, confused.  "You told me at the time, and you said that you were doing a lot better with this new stuff."

"I am.  I'm feeling a lot better, and not suffering the side effects like before  ...."  She paused.

"But?"

"But the doctor warned me to avoid alcohol.  She said the drugs can make me very sleepy if I mix them with booze.  I would really like to share a bottle of wine with you.  With all the stress of being here, it would help me relax, but I don't want to be out cold and spoil our chance of a night of passion."

"I'll make you a promise," I said, trying hard to get her to stop worrying.  "Enjoy a drink with me, relax, and if I have to undress you and put you to bed after, that itself will be reward enough for me."

After six hours driving and a couple of drinks, I didn't think I'd be capable of much else tonight, but I wasn't going to dampen the mood.

It was over breakfast the following morning that Elaine confessed she couldn't remember anything beyond me pouring her a second glass.

"Was I embarrassing?"  She asked.

"Apart from standing on the table and taking a piss in the ice bucket, no."

The innocent, sheepish look turned into a dark glare.

"You're teasing me.  Right?" 

"Of course I'm teasing you," I laughed. "No, you didn't do anything embarrassing.  You were giggling, but no more than we usually do when we're together and I was pleased to see you relaxed and happy.  You were a bit unsteady on your feet walking back to the room, but you managed to undress without too many problems.  It's just that we were still in the lift but thankfully there was no-one in the corridor to see you."

Elaine's face turned pink.  One of the many reasons I loved to tease her was that I found that easy innocence a huge turn on.  I considered myself very lucky to have discovered how base and abandoned she could be when it came to sex, but to the outside world, she was and always would be a perfect lady.  Sadly I wasn't able to keep a straight face for more than a few seconds, which resulted in me getting kicked on the shin.  Hard.

"You got undressed in the bathroom," I confessed.  "You would have been happy to leave your clothes in a heap in the bath, but other than that, you were as good as gold.  I did have to help you get into bed, and despite the fact I was still fully dressed you did say you wanted me to fuck you."

"And did you?  Fuck me?"

"As tempting as the invitation was, I went back to the bathroom to tidy up and brush my teeth.  By the time I got back to bed, you were sound asleep, so no, we didn't fuck last night.  I did make the most of cuddling up next to you, but that was all."

"Yes, you had your arms round me when I woke up this morning.  And you had an erection."  The last comment brought back that little bit of colour to Elaine's cheeks.  "You could have fucked me last night, even if I was out cold.  I want you to enjoy these few days we have together.  You could have done anything you wanted.  I wouldn't have minded."

That particular strand of conversation came to an abrupt close when a waiter brought a young family to the adjacent table.  They were however words that would stay in my head.  It had been a long time since I had seen Elaine naked, or had such an opportunity, but she still had an incredible body and still turned me on.  I was not in the least surprised to have woken with a hard-on.

The rest of the day was long and tedious, but no worse than either of us expected.  Elaine decided it better she deal with the solicitors and family on her own, rather than explain to her cousins who I was.  I hang about in coffee shops and later in the car reading my book.  After she was finished we took the half-hour drive to the coast, had a walk along the beach and sat and ate fish and chips on the promenade while watching the sun go down.  It was still early when we got back to the hotel.  I suggested we go to the bar and enjoy a drink before bed.

"Are you trying to get me drunk again?"

"No," I protested, but couldn't help blush.

The words spoken over breakfast had stuck in my mind.  Apart from that one brief affair, my sex life had been spectacularly unadventurous and I will admit, the idea of fucking Elaine while she was unconscious held a strange sort of appeal.  I wasn't sure if it was just for the pleasure of trying something different, or if it spoke of something far deeper and darker, but I'd come to the conclusion that I would if the opportunity arose.

"Ok," she said, half smiling, half laughing, "I'll believe you, but I'm only having one small glass.  I want to remember at least one night of being with you."

We found a quiet corner with our drinks and as usual, settled into easy conversation.  With sex already at the front of our minds, it was no surprise that most of what we talked about were reminiscences; what we had once enjoyed, and what we would like to do.  It wasn't long before our plan for a relaxed drink turned into a rather desperate rush to get back to the room.

Elaine was out of her clothes a lot quicker than I and lay down on the bed invitingly.  I have to admit I was torn.  Part of me wanted to just bury my cock deep inside that sweet hot cunt.  Knowing that there was now no risk of her getting pregnant (she was post-menopause), that I could fuck her bareback and cum inside her for the first time ever, was a taunt I could hardly resist, but there were other pleasures I wanted to remind her of. 

I crouched on my knees between her parted legs and leaned forward.  The first lick brought back a flood of memories, her juices sticking to my tongue.  While my mouth sought her hardening clitoris, my fingers slid easily into her vagina, and while I sucked and teased with my teeth, I finger fucked her, at first slow, then harder and faster.

When I thought I was going to bring Elaine to a climax, she sat up suddenly and pushed me across the bed.  Forcing me onto my back, she crouched across my face and leaned forward, taking my now throbbing cock into her mouth.  I'd almost forgotten how much she enjoyed giving oral, and how good she was.  The sensations now flowing through my body were wonderful, heightened by the closeup view of her now dripping pussy lips and ass.

Movement was now a little more awkward, but I resumed licking, inserting my tongue between those puffy lips and into the outer reaches of her vagina.  Every now and again, she would stop sucking me and sit up, almost forcing me to put my tongue against her tight puckered ass.  It was a first for me, but needless to say, I didn't object.  If I could have reached, I would have happily inserted my tongue into her anus.

I could sense from the sound of Elaine's breathing and the loud sighs that she was close to an orgasm.  As she returned to sucking my cock, I went back to biting on her swollen bud.  I managed to free one arm and again inserted two fingers into her cunt, this time pushing down against her bladder.  That took her over the top.  She came.  As I felt the muscles of her vagina pulse and squeeze against my fingers, bodily fluids flowed and squirted over my face and into my mouth.  I could taste her cum and her wee.  It started to sting my nostrils but far from being unpleasant, it was wonderful.  I couldn't imagine how I'd lived for three score years and never experienced such bliss.

When Elaine climbed off me, I took the opportunity to run to the bathroom to wipe my face.  When I returned, I could hear that Elaine’s breathing had changed; from that rapid chaos of orgasm into something soft and even.  I don't think she had completely fallen asleep at that point, but I could tell she was close.

Again I was torn.  I knew she had not had an easy day, and the simple fact that I cared made me want to just pull the covers up and let her rest, but I was horny.  I knew that Elaine wouldn't have cared if I'd lay next to her in bed, masturbating until I came but I needed more.  I wanted to fuck her, and remembering her words from breakfast, decided that was exactly what I was going to do.

She had already turned partly onto her side.  It would have been relatively easy to turn her onto her back, and while I thought missionary style had all sorts of advantages, not risking waking her fed into my fantasies.  I put one of the pillows in front of her, gently persuaded her to roll into it, and lifted her knees into a more foetal position.  The only movement she made not orchestrated by me suggested she was just getting comfortable.  She was sleeping.  

I walked round the bed.  Seeing her exposed cunt, her bum cheeks slightly parted and that beautiful tight, puckered hole was magical.  I couldn't resist holding my cock and pulling the foreskin back, imagining where that purple swollen head was going.  I couldn't remember being more aroused or excited about fucking someone, ever.

I lay down behind this beautiful, sexy woman and allowed myself the joy of exploring with my hands, fingers first caressing the soft flesh of her body, wandering slowly down.  I reached between her legs, sliding between her wet cunt lips, feeling the heat of her vagina.  I slid my body and curved my spine, trying to get my cock in a position where I could penetrate that sweet, welcoming pussy but realized it was impossible.  I would have had to be hanging off the edge of the bed and even then I thought Elaine’s legs may still be in the way.

I got up and walked back round the bed, thinking I would somehow get her to move but could see she was now in a deep sleep.  I wasn’t sure whether my motivation was selfish or selfless but it felt wrong to now be risking waking her.  I decided that if I couldn’t fuck and cum inside  Elaine, I might at least be able to cum over her.

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I lay back down behind her, one hand gently massaging the end of my now throbbing cock, the other back under her body fingering and parting her wet pussy lips.  She was still wet, and hot.  From the position I was laying in I couldn’t get more than the end of my finger inside her vagina, but like that, I started to finger fuck Elaine, her cunt making soft, squelchy noises as I moved in and out.

With my other hand, I positioned my cock between the cheeks of Elaine’s beautiful ass, gently rubbing the shaft and sliding the head up and down between the soft flesh.  Now I should probably stress that Elaine and I had never indulged in anal sex.  It wasn’t that she’d ever said she didn’t like it or wasn’t willing, it just never came up.  Equally, I wasn’t sure at that point, I’d made a conscious decision to fuck her ass hole.  My actions just seemed to flow.

While still jerking my cock, I pulled back my other hand back, slid my finger over her tight bum hole and pushed it into her anus.  Still damp from her orgasm, and my finger wet from her cunt, it slid in easily.  I did wonder whether the feeling would wake her, but there was no movement.  One finger was replaced with two, slowly pushing deeper, allowing my knuckle to stretch the sphincter muscles, curling my fingers to explore her insides.

Feelings were racing through my mind and body.  I was getting close to having an orgasm, I needed that release.  The problem was cumming over Elaine no longer seemed to make sense.  I wanted to share this with her in a much more intimate way, I wanted to fill her with my seed.  I started to wipe my own saliva over the end of my cock, and then into the crack of Elaine’s ass.  

I then returned to holding my cock, pulling the foreskin back hard, sliding it once again between those beautiful bum cheeks, this time more easily.  I soon found that tight hole and pushed gently.  I felt it yield.  I waited a moment to see if Elaine would wake if I was causing her pain, but again there was nothing.  I assumed her relaxed state was making this easier.

The second gentle push seemed to get me no further, but with the third, I felt the head of my cock pass through that tight muscle and into Elaine’s rectum.  I could feel that vice-like grip around me.  I pushed again, going deeper, and again deeper still.  Then with half the length of my cock inside her ass, that tightness and thrill took me over the edge.  I came.

My wife and I had stopped having sex for some time, so the most sexual pleasure I’d had recently was in the company of my right hand.  I’d got used to reaching an orgasm like that, but it was never particularly satisfying, and it was never more than a dribble.  Reaching a climax while fucking Elaine, and in particular fucking her bum, was very different.

I felt my penis pulse twice while I was inside her, shooting my semen somewhere deep into her bowels, but as I withdrew and the head of my cock was pushed from her anus, I continued to cum, spraying my hot sticky fluid over her bum-cheeks and thigh.  I don’t remember having an orgasm that strong or that long, ever.  

I remembered the days that Elaine and I would fuck like sex-starved teenagers, desperate for each-others bodies at whatever opportunity.  There were times when I had no condoms but unable to restrain our desires, I’d pull out and ejaculate over her belly.  She loved it.  She adored the feeling and sight of being covered in a man’s cum.  With that in mind, I took photos of what I’d done with my phone, making a mental note to delete them before returning home.

The following morning the euphoria of that evening had turned on its head.  I felt guilty.  It felt wrong to have fucked Elaine without her explicit consent, particularly as I'd fucked her ass.  I felt as though what I'd done was abuse because she was sleeping and not actively participating.  I was ashamed, and apparently that showed.

"Please tell me what's wrong," Elaine asked over breakfast.  "You haven't said a word, and you look as though you don't want to be here with me." 

"I'm sorry, I do want to be here with you, it's just... "

"You feel guilty that we're having sex, that your cheating again?"  Her voice sounded more concerned than angry.

"That is part of it I suppose," I said thoughtfully.  "This has reminded me how much I enjoyed sharing you, how much I enjoyed snatching those brief moments of passion.  That is going to be hard to live with when we get back.  Neither of us enjoy the freedom or opportunities we used to have.  But the bit I'm really struggling with is that I did fuck you last night."

It was clear from her expression that she didn't understand.  I could still hear her saying that I could have done anything I wanted, that she wouldn't have minded, but somehow I felt I had crossed a line.  

"How much do you remember?" I asked.

"I can remember going back to the room and being on the bed naked.  It does start to get a bit vague after that.  I think we started doing sixty-nine, but I really don't know if that was just me dreaming.  Please just tell me what happened so I can figure out why you seem so worried."

So I told her, exactly as I have told you.  Every touch, every movement, every thought and feeling.  As the story unfolded, I grew more nervous, thinking she would be upset, worrying she would be angry.  I pushed my half-eaten breakfast away from me, unable to face taking another mouthful.

I finished the tale, half expecting Elaine to walk away, but she just sat there, smiling.  In all the years we had known each other we had never had a fight.  Not even a difference of opinion, and I genuinely don't know how I would have handled an upset now.  I will admit that I was troubled by the lengthy silence, but glad there were no harsh words.

"How many times have I told you that I love you?" She asked eventually.

"Most days over the past twenty years," I said nervously, not knowing if this was a rhetorical question.  "I'm not sure I could work out an exact total, but it's a lot."

"It is a lot, but apparently you still haven't got the message that I would do anything for you.  I will tell you one more time in the hope that it sinks in.  I love you.  I don't mind that you fucked me while I was asleep last night.  I don't mind that you fucked my bum.  I don't mind that you came all over me.  I am very pleased that you did and it matters to me that you enjoyed it.”  Her voice turned more sheepish when she added  “My only regret is that I wasn't conscious to see it.  You know how much I love being covered in cum."

I pulled the phone out of my pocket and showed her the photos.  Elaine's face turned pink and her smile became a grin.

"Are you sure you were the only person to cum over me.  There's an awful lot of the stuff."  She spoke as though she had suddenly developed a stutter.  She was shocked but in a good way.  I could tell she was getting aroused.

"I know.  I don't think I have ever cum like that before.”

Our conversation was again brought to an abrupt halt as the same young family was ushered to the adjacent table, Mum and Dad this time engaging us in polite hello’s.  Elaine excused herself to go to the ladies.  I was just trying to work out if I’d regained enough of an appetite when my phone pinged.  It was a text message.

‘I’m in the toilet.  You made me horny and very wet.  Do you want to come and fuck me?’

‘Yes.’ I replied. ‘Ladies toilet or bedroom?’  Suddenly the fact that I was hungry no longer mattered.

‘Bedroom.  Do I have to put my panties back on?’

‘No.  Meet me by the lift.’

I finished the last mouthful of coffee and almost ran out of the restaurant.  Elaine was waiting for me looking hot and flustered.  Knowing she had been sat in that toilet, thinking about what we’d said at breakfast and that she’d been playing with herself, was incredibly erotic.  As the lift door closed, I slid a hand under her skirt and up between her legs.  Even her thighs were damp.

Back in the room we virtually tore clothes off each-other.  I know at least one of my shirt buttons came loose and was forever grateful that Elaine’s top slid easily over her head.  Unhooking a bra was never something I’d gained proficiency at, and my aging, slightly arthritic fingers weren’t going to make the task quicker, so that stayed on.  I know it wouldn’t get in the way of groping her tits, but for the moment my focus was somewhere else.

Elaine jumped on to the bed and spread her legs wide, almost pulling me on top of her.  Under any other circumstances, there might have been some foreplay, some fondling or oral, but we both seemed to read what we wanted and needed.  She was already wet, and I was already hard.  With just a little bit of guidance necessary, I plunged my cock deep into Elaine’s hot waiting cunt.

With arms wrapped lovingly around me, with breasts pushing against my chest, being inside Elaine once more was perhaps the most exquisite feeling I could imagine.  And this was no slow, caring movement, this was hard and hungry.  We were fucking like the world was about to stop.  I managed to get my arms under Elaine’s legs and pin them under my shoulders, forcing her to arch her back.  I slid even deeper into her.  I could feel the head my pubic bone pressing into the soft flesh of her labia and clitoris.  I could feel my ball sack slapping against her perineum.  I could feel the head of my cock pressing into her stomach.

It wasn’t long before I felt that spasm ripple through Elaine’s body, heard the sharp intake of breath and long guttural moans as she reached her first climax.  I continued to fuck her, harder and faster.  I could feel fluids being squeezed from Elaine’s vagina and perhaps her bladder making me wet, and making the two of us squelch as our bodies collided.  

When Elaine came a second time, the muscles in her vagina squeezing, it took me over the top.  I held still and felt my cock pulse, delivering my hot sperm into her womb, filling her with my seed.  I knew that after the previous night, I would unlikely have produced as much cum, but my orgasm seemed to last just as long.

Eventually, I withdrew my cock and we collapsed into a heap of random arms and legs across the bed.  Neither of us had the energy to roll over and embrace, but I was happy to hold hands and enjoy the feel where our bodies happened to touch.  I think we might have stayed like that forever but our reverie was interrupted by a knock, accompanied by that call of ‘Housekeeping.’  I knew the one thing we didn’t do in our desperation was bolt the door.  I don’t think I have ever run so quick.

“Can you give us an extra hour,” I pleaded, trying to hide my naked form around the half-open door.   It was a remarkably pretty young girl, making my now obvious predicament all the more embarrassing.

“Of course sir.”  She smiled knowingly.  “Please take your time.  I’ll come back later.”

It was sadly a reminder that no matter how good the sex was with Elaine, that it would always involve that element of secrecy and shame.  It would always be something we would have to hide from the world.  After twenty years I had grown very philosophical about the affair I’d had with Elaine, but that housemaid, albeit innocently, had stirred all those feelings and emotions once more.

“A penny for them?”  Elaine asked.  We had by then been on the road for a good two hours.

“Sorry?”

“You’ve hardly said a word since we checked out of the hotel.  I was wondering what’s bothering you.  Do you regret fucking me again?”

“No,” I said, trying hard to watch the road.  “I could never regret what we did.  It was probably the best sex I’ve had, ever.  How could I regret that.”

“But?”  She knows me too well, knew the tone of my voice.  She is perhaps the one person I can’t hide from.

“But,” I started hesitantly, not even sure of what words to use.  “I’m going to miss it.  I hard a hard time with the decisions we came to all those years ago.  I don’t regret them and I’m glad of what grew out of those decisions, but it was difficult at the time, and it is going to be just as difficult now.”

“I know.” She said after a long pause.  “I will miss it too.  I often miss having you in my bed with me.  Not just because the sex is good, but just having you close by.  You are good to have around, you proved that by helping me these past two days, and you’re good for me.  We’ve learnt how to deal with staying friends, perhaps we can learn how to stay lovers too.”

“It got complicated before, and neither of us handled that well.”

“I know,” she said, sounding surprisingly upbeat.  “But then neither of us imagined that opportunities like this might come our way.  If it’s happened once, why wouldn’t it happen again?”

That’s where my story ends.  We both returned to domesticity with our respective spouses, no-one (with the possible exception of one maid) any the wiser as to what happened during that forty-eight hours.  I would say our friendship returned to what it was, but there was that shared memory every time we spoke, that added flirtation if we messaged each-other, that hope that we would get to do it all again.

Published 
Written by Nonimouse
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